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Ian R Gould  > igould@asu.edu CHM 234 : General Organic Chemistry II  > Spring 2012
 CHM 234/238
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This class uses "gapped" lecture notes. The idea is that the tedious part of the note-taking is done for you, so that you spend less time writing in lecture, and more time listening and learning. The gaps represent those parts of the material that I think need to be emphasized, or that you need to learn how to to write and/or draw yourself. The gaps also help to keep you awake at 7:30 AM!

   

After we have finished each section of the notes in class, I will post my completed version so that you can make sure that you have no gaps or mistakes.

The "gapped" versions of the notes are given below, in the form of .pdf files. You can either print these and bring them to lecture, or you can save money by purchasing the entire gapped notes set from The Alternative Copy Shop, which is at the southwest corner of Mill Ave. and 10th street. Give them a call to order or before you go to make sure that they have some copies in stock, (480) 829-7992. The cost should be ca. $30.

click here for the condensed version of this summary, including direct links to the gapped and completed versions of the notes

Section   Relevant Section in
Smith 3rd Edition Textbook
    
A Introduction to Retrosynthesis  
    1. Summary Of Reactions From First Semester Organic N/A
      1.1 Synthesis of Halides (Bromides) 15.6, 15.7, 15.10, 10.9, 15.13
      1.2 Synthesis of Alkenes 8.4, 8.5
      1.3 Alkenes From Alcohols 9.8
      1.4 Synthesis of Alcohols 10.16
      1.5 Synthesis of Dibromides 10.13
      1.6 Synthesis of Alkanes 12.3
      1.7 Synthesis of Epoxides 12.8
      1.8 SN2 Reactions 7.19
    2. Multi-Step Synthesis 7.19, 10.18
    3. Retrosynthetic Analysis ; The Synthon N/A
    4. SN2 Reactions Revisited : Practice Doing Reactions in Reverse in Reverse 7.19
    5. Putting It All Together : A Retrosynthetic Strategy 10.18, 11.12
    
B Alkynes: Developing Synthetic Methods  
    1. Nomenclature 11.2
    2. Structure and Properties 11.1
      2.1 Alkyne Acidity 11.11
      2.2. Alkyne Acidity in Water and Ammonia N/A
    3. Preparation of Alkynes 11.5
    4. Reactions of Alkynes 12.5
      4.1 Addition of Hydrogen (Reduction) 12.5
      4.2 Addition of H-X, X2 etc. 11.7, 11.8
      4.3 Addition of H2O 11.9
      4.4 Formation of trans-Alkenes 12.5
    5. Acetylide Anions : Retrosynthesis and Carbon-Carbon Bonds 11.11
      5.1 Addition to Alkyl Halides 11.11A
      5.2 Addition to Carbonyls and Epoxides 11.11B
      5.3 Examples in Synthesis 11.12
    6. Summary of Reactions N/A
    
C Alcohols : Oxidation and Reduction  
    1. Nomenclature 9.3
    2. Alcohol Acidity N/A
      2.1 Review of Substituent EFfects 18.6
    3. Oxidation Reduction Definition 12.1
    4. Preparation of Alcohols 9.6
      4.1 Review of Reactions That We Have Already Seen 9.6
      4.2 Hydride Reduction of a Carbonyl Group 20.4
    5. Reactions of Alcohols 10
      5.1 Oxidation 12.12
      5.2 Formation of Alkyl Halides 9.11
      5.3 Formation of Tosylate Esters 9.13
      5.4 Dehydration 9.8
    6. Summary of Reactions N/A
    
D Organometallic Reagents : Carbon-Carbon Bonds  
    1. Carbon-Metal Bonds 20.9
    2. Nucleophilic Addition Reactions 20.10, 20.11
    3. Organometallics in Synthesis N/A
    4. Organometallics: Summary of Reactions N/A
    
E Ethers and Epoxides: Reactions with Bronsted Acids and Bases  
    1. Terminology and Properties 9.1
    2. Nomenclature 9.3
    3. Preparation of Ethers 9.6
      3.1 Williamson Ether Synthesis 9.6
      3.2 Preparation Methods for Ethers/Epoxides Seen Before 12.8
    4. Reactions of Ethers/Epoxides 9.7B
      4.1 Cleavage of Ethers Using Acid 9.14
      4.2 Acid Catalyzed Opening of Epoxides 9.15B
      4.3 Base Catalyzed Opening of Epoxides 9.15A
      4.4. Examples in Synthesis N/A
    5. Summary of Reactions N/A
    
F Conjugated Systems : Return to Molecular Orbital Theory  
    1. Conjugated Systems and Resonance 16.1 - 16.6
    2. Reactions of Allyl Systems : Conjugated Intermediates 15.10
    3. Reactions of Dienes : Kinetic and Thermodynamic Control 16.10
    4. Diels-Alder Reaction : Cycloaddition 16.12 - 16.14
    5. Pi-Molecular Orbitals 17.9
      5.1 Rules for Constructing Pi Molecular Orbitals N/A
      5.2 Pi-Molecular orbitals of Ethylene 7.8, 29.2
      5.3 Pi-Molecular orbitals of Butadiene N/A
      5.4 Pi-Molecular orbitals of Allyl Systems N/A
      5.5 Relative Energies of Pi-Molecular Orbitals N/A
      5.6 Origin of Conjugation/Resonance Stability N/A
    6. Frontier Molecular Orbital Theory and Pericyclic ReactionsN/A
    7. Aromatic Transition State Theory and Pericyclic Reactions N/A
    8. Summary of Reaction Types N/A
    
G Aromaticity: Stability and Instability in Cyclic Pi-Systems  
    1. Huckel Rule 17.7, 17.9
    2. Aromatic Ions 17.8D
    3. Aromatic Heterocycles 17.8C
    4. Other Examples 17.8
    
H Reactions of Benzenes: Electrophilic Aromatic Substitution  
    1. Notation, Structure and Nomenclature 17.2, 17.3
    2. Miscellaneous Reactions of Benzenes 18.14
      2.1 Reductions: Addition of Hydrogen 18.14
      2.2 Side-Chain Oxidation 18.14
    3. Electrophilic Aromatic Substitution 18.1, 18.2
      3.1 Halogenation of Benzenes 18.3
      3.2 Nitration of Benzenes 18.4
      3.3 Sulfonation of Benzenes 18.4
      3.4 Alkylation and Acylation of Benzenes 18.5
    4. Reactions of Disubstituted Benzenes 18.7 - 18.11
      4.1 Donating Groups - Activating and Ortho- and Para-Directing 18.9
      4.2 Withdrawing Groups - Deactivating and Meta-Directing 18.9
      4.3 Halogens as Substituents - Deactivating BUT Ortho- and Para-Directing 18.9
      4.4 Predicting Substituent Effects for Multiply Substituted Benzenes 18.9, 18.11
    5. Synthesis of Substituted Benzenes 18.12, 18.15
    6. Nucleophilic Aromatic Substitution N/A
    7. Summary of Reactions N/A
    
I Aldehydes and Ketones : Nucleophilic Addition  
    1. Structures and Nomenclature 20.1
    2. Synthesis of Aldehydes and Ketones : Review of "Old" Methods 21.6
    3 New Synthesis Methods for Aldehydes and Ketones : Introduction to Acid Catalyzed Mechanisms N/A
      3.1 Using 1,3-Dithiane N/A
      3.2 Grignard Addition to Nitriles 22.18C
      3.3 Hydrolysis Reactions 22.14B
    4. Reactions of Aldehydes and Ketones 21.7
      4.1 Comparing Reactivities of C=C and C=O Bonds N/A
      4.2 Strong and Weak Nucleophiles 21.7
      4.3 Relative Reactivities of Aldehydes and Ketones N/A
      4.4 Reactions with Grignard and Acetylide Reagents as Strong Nucleophiles (Review) 11.11, 20.9, 20.10, 20.11
      4.5 Reactions with Hydride Reagents as Strong Nucleophiles (Review) 21.8
      4.6 Hydrate Formation: Hydroxide as a Strong Nucleophile, Water as a Weak Nucleophile 21.13
      4.7 Factors Controlling Water and Other Addition Equilibria 21.13A
      4.8 Acetal and Hemiacetal Formation: Alkoxide as a Strong Nucleophile, Alcohol as a Weak Nucleophile 21.14
      4.9 Controlling Reversibility in Acetal Formation : Introduction to Protecting Groups 21.15, 21.16
      4.10 Amines as Intermediate Nucleophiles 21.11
      4.11 Complete Reduction of C=O (Clemmenson and Wolf-Kischner, Revisit) 18.14B
      4.12 Wittig Reaction. Makes a C=C bond in Two Steps 21.10
    5. Summary of Reactions N/A
    
J Enols and Enolates : Acidities of Carbonyls  
    1. Enolizable Hydrogens 23.2, 23.3, 23.5
    2. Alkylation and Halogenation Reactions of Enols/Enolates 23.6
      2.1 Alpha-Halogenation 23.7
      2.2 Alkylation of Aldehydes/Ketones via Enamines/Enolates 23.8
      2.3 "Template Synthesis" Using Alkylation of the Malonic Ester Enolate 23.9
    3. Aldol and Claisen Reactions of Enols/Enolates 24.1, 24.5
      3.1 Aldol Condensation of Aldehydes/Ketones 24.1 - 24.4
      3.2 Rationalizing the Various Possible Products, How do Carbonyls Know What to do? N/A
      3.3 Crossed Aldol Condensations 24.2
      3.4 Claisen Condensations : Enolates of Esters 24.5, 24.6
      3.5 Aldol/Claisen Summary N/A
      3.6 Aldols/Claisens in Reverse N/A
    4. Summary of Enol/Enolate Reactions N/A
    
K Carboxylic Acids : Organic Acids  
    1. Nomenclature 19.2
    2. Factors Controlling Acidity 19.9 - 19.11
    3. Preparation of Carboxylic Acids N/A
    3.1 "Old" Methods 19.7
      3.2 New Methods 20.14A, 22.18A
      3.3 Carboxylic Acid Synthesis StrategiesN/A
      4. Reactions of Carboxylic Acids N/A
      4.1 Fischer Esterification 22.10C
      4.2 Formation of Acid Chlorides 22.10A
      4.3 Reduction with LiAlH4 20.7B
    5. Summary of Reactions N/A
    
L Carboxylic Acid Derivatives : Addition/Elimination  
    1. Nomenclature 22.3
      1.1 Acid Halide Nomenclature 22.3A
      1.2 Anhydride Nomenclature 22.3B
      1.3 Ester Nomenclature 22.3C
      1.4 Amide Nomenclature 22.3D
      1.5 Nitrile Nomenclature 22.3E
      1.6 Some Common Names of Acid Derivatives 22.3
    2. Reactivity Order for Acid Derivatives 22.7
    3. Interconversion of Acid Derivatives : Nucleophilc Acyl Substitution 22.7
      3.1 Formation of Anhydrides 22.8
      3.2 Formation of Esters 22.8, 22.9
      3.3 Formation of Amides 22.8, 22.9, 22.10
    4. Hydrolysis Reactions of Acid Derivatives N/A
      4.1 Acid Chlorides and Anhydrides N/A
      4.2 Esters, Require Acid or Base Catalysis 22.11
      4.3 Amides Require Forcing Conditions 22.13
      4.4 Nitriles Also Require Forcing Conditions 22.18A
    5. Reduction of Acid Derivatives 20.7A, 20.7B
    6. Synthesis Using Acid Derivatives 22.7
    7. Summary of Reactions Involving Acid Derivatives N/A
    
M Amines : Organic Bases  
    1. Nomenclature 25.3
    2. Amines as Bases 25.9, 25.10
    3. Synthesis of Amines 25.7
      3.1 Amine Synthesis Involving Nucleophile Addition/Reduction 25.7
      3.2 Synthesis of Amines by Reductive Amination 25.7C
    4. Reactions of Amines N/A
      4.1 Amines as Nucleophiles 25.11
      4.2 Hofmann Elimination 25.12
      4.3 Diazonium Salts 25.13
    5. Some Amine Reactions in Synthesis N/A
    6. Summary of Reactions Involving Amines N/A

click here for the condensed version of this summary, including direct links to the gapped and completed notes